4-Methylmorpholine → Phenylmethyl (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-3-{[(4-{[(phenylmethyl)oxy]carbonyl}phenyl)amino]carbonyl}-1-pyrazolidinecarboxylate

HRID 1396959

Reaktionsgleichung

Reaktionsgleichung von HRID 1396959
[CH:1]1([CH2:6][C@H:7]([CH2:28][N:29]([CH:38]=[O:39])[O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:8]([N:10]2[C@H:14]([C:15](O)=[O:16])[CH2:13][CH2:12][N:11]2[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.CN1CCOCC1.F[B-](F)(F)F.COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.[NH2:69][C:70]1[CH:85]=[CH:84][C:73]([C:74]([O:76][CH2:77][C:78]2[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=2)=[O:75])=[CH:72][CH:71]=1>C(#N)C>[CH:1]1([CH2:6][C@H:7]([CH2:28][N:29]([CH:38]=[O:39])[O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:8]([N:10]2[C@H:14]([C:15]([NH:69][C:70]3[CH:85]=[CH:84][C:73]([C:74]([O:76][CH2:77][C:78]4[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=4)=[O:75])=[CH:72][CH:71]=3)=[O:16])[CH2:13][CH2:12][N:11]2[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1

Komponenten

6

Edukt 4

HCID 79724-MethylmorpholineHCID 98488Benzyl p-aminobenzoateHCID 116312684-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium tetrafluoroborateHCID 86706346HCID 86706346, Verbindung

Produkt 1

HCID 86706391Phenylmethyl (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-3-{[(4-{[(phenylmethyl)oxy]carbonyl}phenyl)amino]carbonyl}-1-pyrazolidinecarboxylateAusbeute 79,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-1-{[(phenylmethyl)oxy]carbonyl}-3-pyrazolidinecarboxylic acid (300 mg, 0.558 mmol) in acetonitrile (10 mL) under N2 at 0° C. was added 4-methylmorpholine (123 mg, 2.2 mmol), followed by 4-[4,6-bis(methyloxy)-1,3,5-triazin-2-yl]-4-methylmorpholin-4-ium tetrafluoroborate (366 mg, 1.116 mmol). The mixture was stirred for 1 h and to this mixture was added phenylmethyl 4-aminobenzoate (191 mg, 0.837 mmol). The mixture was stirred at rt overnight. The mixture was concentrated, and the residue was purified by flash column chromatography eluting with petroleum ether/ethyl acetate (5:1 to 3:1) to provide the title compound (330 mg).

Aufarbeitung

  1. stirringThe mixture was stirred at rt overnight
  2. concentrationThe mixture was concentrated
  3. customthe residue was purified by flash column chromatography
  4. washeluting with petroleum ether/ethyl acetate (5:1 to 3:1)

Quellen und Nachweise

ORD-Eintrag
ord-673b094275fd46dbac602e976ca39825
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901119B2

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